Oleuropein

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Oleuropein
Names
IUPAC name
(4S,5E,6S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethylidene-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy}-4H-pyran-3-carboxylic acid methyl ester
Other names
2-(3,4-Dihydroxyphenyl)ethyl [(2S,3E,4S)-3-ethylidene-2-(β-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl]acetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.046.466 Edit this at Wikidata
  • InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1 checkY
    Key: RFWGABANNQMHMZ-ZCHJGGQASA-N checkY
  • InChI=1/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
    Key: RFWGABANNQMHMZ-ZCHJGGQABE
  • O=C(OCCc1ccc(O)c(O)c1)C[C@H]2C(=C/C)\[C@@H](O\C=C2\C(=O)OC)O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO
Properties
C25H32O13
Molar mass 540.51 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oleuropein is a glycosylated seco-iridoid, a type of phenolic bitter compound found in green olives, olive leaves, and argan oil.[1][2][3] During processing of inedible green olives for human consumption as table olives, oleuropein is removed from olives by immersion in lye.[4]

Basic research

In preliminary laboratory research, oleuropein had activity as an agonist of the G-protein estrogen receptor.[5] Other basic research is examining whether oleuropein and other olive polyphenols have pharmacological properties and potential anti-disease activity,[6] none of which is proved to exist in humans as of 2017.[2]

See also

References

  1. ^ Bendini, A; Cerretani, L; Carrasco-Pancorbo, A; Gómez-Caravaca, A. M.; Segura-Carretero, A; Fernández-Gutiérrez, A; Lercker, G (2007). "Phenolic molecules in virgin olive oils: A survey of their sensory properties, health effects, antioxidant activity and analytical methods. An overview of the last decade". Molecules (Basel, Switzerland). 12 (8): 1679–719. doi:10.3390/12081679. PMID 17960082.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  2. ^ a b Rigacci, S; Stefani, M (2016). "Nutraceutical Properties of Olive Oil Polyphenols. An Itinerary from Cultured Cells through Animal Models to Humans". International Journal of Molecular Sciences. 17 (6): 843. doi:10.3390/ijms17060843. PMC 4926377. PMID 27258251.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  3. ^ "Phenols and Polyphenols from Argania spinosa". American Journal of Food Technology. 2 (7): 679–683. 2007. doi:10.3923/ajft.2007.679.683. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  4. ^ "How olives are made". California Olive Committee. 2017. Retrieved 5 August 2017.
  5. ^ Prossnitz, Eric R.; Barton, Matthias (2014). "Estrogen biology: New insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207. PMC 4040308. PMID 24530924.
  6. ^ Taamalli, A; Arráez-Román, D; Zarrouk, M; Valverde, J; Segura-Carretero, A; Fernández-Gutiérrez, A (2012). "The occurrence and bioactivity of polyphenols in Tunisian olive products and by-products: A review". Journal of Food Science. 77 (4): R83–92. doi:10.1111/j.1750-3841.2011.02599.x. PMID 22352878.
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